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The Best Chelsea Boots You Can Buy

From best-value to best-in-class, our guide to Chelsea boots covers ready-made designs from new brands and bespoke pairs from legacy makers.

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Chelsea boots originated in England in the mid-19th century. Then, they were called "Paddock boots," a short style for equestrian functions. They've only strayed from home — and horse riding — just recently. The elasticized wonders were a staple in mid-’60s London scenes and protected the feet of seemingly every British invader — from John Lennon to Ringo Starr. Recently, they’ve seen a revival on many of menswear’s best-dressed.

What Are Chelsea Boots?

Marked by a slim silhouette, elastic side panels, and heel pull-tabs, the boot has seen reinterpretations in leather, suede, and neoprene, either with crepe, leather or rubber soles. They're a versatile option that's gone largely unchanged since inception, save for material swaps here and there. And while they aren't as in-demand as they were in the mid-2010s — when everyone from Kanye West and David Beckham to Harry Styles and Justin Theroux was wearing theirs — Chelsea boots prove sensible now more than ever. The style emphasizes both aesthetics and comfortability, meeting in a middle ground where both camps — those wearing them for their look and those wearing them for their convenience — are appeased.

How to Wear Chelsea Boots

Further, designers from all over have riffed on the shape over and over and over again, resulting in a rich landscape of iterations to choose from. Whether you're looking for a pair that's polished or preppy (to wear with an Oxford and chinos), with a bit of street cred (to wear with jeans and a hoodie) or suit-friendly (to wear with a, well, suit), here are more than a dozen different Chelsea boots to choose from.


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Best Overall Chelsea Boots
Blundstone BL558 Boots
Best Upgrade Chelsea Boots
R.M. Williams Craftsman Boot
Best Affordable Chelsea Boots
Rhodes Blake Boot
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New Republic Sonoma Suede Chelsea Boot
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Taylor Stitch The Ranch Boot
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Viberg Chelsea Boot
Belstaff Longton Leather Chelsea Boot
Unmarked Chelsea Toro Special Edition
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Oliver Cabell Chelsea Boot
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Oak Street Bootmakers 5504 Chelsea Boot
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Common Projects Suede Chelsea Boots
Diemme Balbi Suede Ankle Boots
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Grant Stone Chelsea Boot
Astorflex Bitflex
Nisolo All-Weather Chelsea Boot
Beckett Simonon Bolton Chelsea Boots
Tecovas The Chance
Clarks Clarkdale Hall Beeswax Leather
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